The Simpsons (1989)

S16E5 Fat Man and Little Boy

Bart creates catchy slogans for T-shirts, which piques the interest of Goose Gladwell, a quirky entrepreneur in novelty gifts. Before long, Bart finds himself thriving as a T-shirt mogul. Meanwhile, Homer starts to feel increasingly sidelined, struggling with his role in the family as Bart takes on the responsibility of the main provider.